Researchers have emphasized the importance of parental involvement in ensuring the educational success of children. Despite the recognized value, some stakeholders continue to struggle to leverage and sustain this partnership, which may encumber students' success. The purpose of this study was to gain an understanding of the factors influencing parental involvement in Jamaican high schools. This qualitative case study sought to unearth the motivational factors influencing parental involvement within a climate of educational accountability in Jamaican high schools. Grounded in Epstein's school-family-community partnership model, this study unearthed some of the differences and similarities of parental involvement within high schools that were described as high and under performing schools and what informed those differences. Sixteen participants from 4 high schools were interviewed using a semistructured interview guide. The data were analyzed thematically and interpreted against Epstein's theory. The findings of this study indicated that all stakeholders in a child's education had mutual interests and influences and an expressed desired to increase their involvement. The motivational factors driving their involvement varied from policies, beliefs, benefits, and personal challenges; parental involvement also differed in quality and quantity across schools and requires creativity in design for greater involvement, accountability, and impact. The strategic utility of these findings can assist in the creation of the home support engagements needed to remove the constraints impeding students and wider school success, thereby guiding students into successful directions, which is the epitome of social change.